Trifluoroacetic acid → HCID 23514103, compound

HRID 353478Notes

Reaction equation

HRID 353478 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:48]=[CH:47][C:12]([CH2:13][N:14]2[C:22]3[C:17](=[C:18]([C:23]([NH:25][CH2:26][CH2:27][NH:28]C(=O)OC(C)(C)C)=[O:24])[CH:19]=[CH:20][CH:21]=3)[C:16]([C:36](=[O:46])[C:37](=[O:45])[NH:38][C:39]3[CH2:40][O:41][C:42](=[O:44])[CH:43]=3)=[CH:15]2)=[CH:11][CH:10]=1>C(Cl)Cl>[NH2:28][CH2:27][CH2:26][NH:25][C:23]([C:18]1[C:17]2[C:16]([C:36](=[O:46])[C:37](=[O:45])[NH:38][C:39]3[CH2:40][O:41][C:42](=[O:44])[CH:43]=3)=[CH:15][N:14]([CH2:13][C:12]3[CH:11]=[CH:10][C:9]([Cl:8])=[CH:48][CH:47]=3)[C:22]=2[CH:21]=[CH:20][CH:19]=1)=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23513969HCID 23513969, compound

Product 1

HCID 23514103HCID 23514103, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.1 ml) is added to a stirred solution of tert-butyl 2-{[(1-(4-chlorobenzyl)-3-{oxo[(5-oxo-2,5-dihydro-3-furanyl)amino]acetyl}-1H-indol-4-yl)carbonyl]amino}ethylcarbamate of Example 9 (50 mg) in CH2Cl2 (1 ml). After stirring at room temperature for 3 h the solvent is removed by roto-evaporation and the residue is taken up with water, adjusting the pH at about 8-9 with 1N NaOH. The precipitate is collected by filtration and thoroughly washed to give N-(2-aminoethyl)-1-(4-chlorobenzyl)-3-{oxo[(5-oxo-2,5-dihydro-3-furanyl)amino]acetyl}-1H-indole-4-carboxamide (25 mg).

Workup

  1. customis removed by roto-evaporation
  2. filtrationThe precipitate is collected by filtration
  3. washthoroughly washed

Sources & evidence

ORD record
ord-278060cb51f54eccbd15fc11362e5eff
Source dataset
uspto-grants-2004_06
Patent number
US06753342B2

Reaction notes

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